diff --git a/lib/workers/notify_annual_renewal.ex b/lib/workers/notify_annual_renewal.ex
index 7c89e23a1..d5a66fbe8 100644
--- a/lib/workers/notify_annual_renewal.ex
+++ b/lib/workers/notify_annual_renewal.ex
@@ -9,19 +9,30 @@ defmodule Plausible.Workers.NotifyAnnualRenewal do
   Sends a notification at most 7 days and at least 1 day before the renewal of an annual subscription
   """
   def perform(_job) do
+    current_subscriptions = from(
+      s in Plausible.Billing.Subscription,
+      group_by: s.user_id,
+      select: %{
+        user_id: s.user_id,
+        inserted_at: max(s.inserted_at)
+      }
+    )
+
     users =
       Repo.all(
         from u in Plausible.Auth.User,
-          join: s in Plausible.Billing.Subscription,
-          on: s.user_id == u.id,
-          left_join: sent in "sent_renewal_notifications",
-          on: s.user_id == sent.user_id,
-          where: s.paddle_plan_id in @yearly_plans,
-          where:
-            s.next_bill_date > fragment("now()::date") and
-              s.next_bill_date <= fragment("now()::date + INTERVAL '7 days'"),
-          where: is_nil(sent.id) or sent.timestamp < fragment("now() - INTERVAL '1 month'"),
-          preload: [subscription: s]
+        join: cs in subquery(current_subscriptions),
+        on: cs.user_id == u.id,
+        join: s in Plausible.Billing.Subscription,
+        on: s.inserted_at == cs.inserted_at,
+        left_join: sent in "sent_renewal_notifications",
+        on: s.user_id == sent.user_id,
+        where: s.paddle_plan_id in @yearly_plans,
+        where:
+        s.next_bill_date > fragment("now()::date") and
+        s.next_bill_date <= fragment("now()::date + INTERVAL '7 days'"),
+        where: is_nil(sent.id) or sent.timestamp < fragment("now() - INTERVAL '1 month'"),
+        preload: [subscription: s]
       )
 
     for user <- users do
diff --git a/test/workers/notify_annual_renewal_test.exs b/test/workers/notify_annual_renewal_test.exs
index 3c0b0fedc..847ffec54 100644
--- a/test/workers/notify_annual_renewal_test.exs
+++ b/test/workers/notify_annual_renewal_test.exs
@@ -39,6 +39,26 @@ defmodule Plausible.Workers.NotifyAnnualRenewalTest do
     assert_no_emails_delivered()
   end
 
+  test "ignores user with old yearly subscription that's been superseded by a newer one", %{user: user} do
+    insert(:subscription,
+      inserted_at: Timex.shift(Timex.now(), days: -1),
+      user: user,
+      paddle_plan_id: @yearly_plan,
+      next_bill_date: Timex.shift(Timex.today(), days: 5)
+    )
+
+    insert(:subscription,
+      inserted_at: Timex.now(),
+      user: user,
+      paddle_plan_id: @yearly_plan,
+      next_bill_date: Timex.shift(Timex.today(), days: 30)
+    )
+
+    NotifyAnnualRenewal.perform(nil)
+
+    assert_no_emails_delivered()
+  end
+
   test "sends renewal notification to user whose subscription is due for renewal in 7 days", %{
     user: user
   } do